2-(2-Ethoxyphenyl)ethaneimidamide hydrochloride → 5-(4-Chlorophenyl)-4-cyclopropyl-2-{[5-(2-ethoxybenzyl)-4H-1,2,4-triazol-3-yl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one

HRID 714686Notes

Reaction equation

HRID 714686 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:15][CH2:14]3)[C:11](=[O:16])[N:10]([CH2:17][C:18]([NH:20][NH2:21])=O)[N:9]=2)=[CH:4][CH:3]=1.Cl.[CH2:23]([O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH2:32][C:33](=N)[NH2:34])[CH3:24]>CN(C=O)C.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:15][CH2:14]3)[C:11](=[O:16])[N:10]([CH2:17][C:18]3[NH:34][C:33]([CH2:32][C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=4[O:25][CH2:23][CH3:24])=[N:21][N:20]=3)[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 666235292-(2-Ethoxyphenyl)ethaneimidamide hydrochlorideHCID 674061412-[3-(4-Chlorophenyl)-4-cyclopropyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetohydrazide

Product 1

HCID 1784661795-(4-Chlorophenyl)-4-cyclopropyl-2-{[5-(2-ethoxybenzyl)-4H-1,2,4-triazol-3-yl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
200 °C

Procedure

50 mg (0.16 mmol) of the compound from Example 21A were taken up in 1 ml of DMF, 52 mg (0.24 mmol) of 2-(2-ethoxyphenyl)ethaneimidamide hydrochloride were added and the mixture was stirred in a microwave oven at 200° C. for 1 h. After cooling, the reaction was diluted with about 1 ml of methanol and the solution was directly separated by preparative HPLC [Method 19]. This gave 21 mg (28% of theory) of the title compound.

Workup

  1. temperatureAfter cooling
  2. customthe solution was directly separated by preparative HPLC [Method 19]

Sources & evidence

ORD record
ord-d76d5c22e26345eb8b66c1302550e23e
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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